Molecular design of a PET-based chemosensor for uronic acids and sialic acids utilizing a cooperative action of boronic acid and metal chelate

Tetrahedron

Volumn 54, Issue 13, 1998, Pages 3125-3140

  Yamamoto, Masashi ^a   Takeuchi, Masayuki ^a   Shinkai, Seiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; SIALIC ACID; URONIC ACID;

ARTICLE; BINDING AFFINITY; CARBOHYDRATE ANALYSIS; CHEMOSENSITIVITY; ELECTRON TRANSPORT; INFLUENZA VIRUS; PRIORITY JOURNAL; STOICHIOMETRY;

EID: 0032568352     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00057-X     Document Type: Article

References (32)

1. (1) (a) Touster, O. Annu. Rev. Biochem., 1962, 31, 407.
2. (b) Chatterjee, I. B. World Rev. Nutr. Diet., 1978, 30, 69.
3. (2) (a) Weis, W.; Brown, J. H.; Cusack, S.; Paulson, J. C; Skehel, J. J.; Wiley, D. C. Nature, 1988, 333, 426.
4. (b) Sayter, N. K.; Glick, G. D.; Crowther, R. L.; Park, S.-J.; Eisen, M. B.; Skehel, J. J.; Knowles, J. R.; Wiley, D. C. Proc. Natl. Acad. Sci. USA, 1992, 89, 324
5. (3) Cohen, S. S. J. Biol. Chem., 1953, 201, 71 and references cited therein.
6. (4) Dische, Z. J. Biol. Chem., 1953, 204, 983 and references cited therein.
7. (5) For comprehensive reviews see (a) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Supramol. Chem., 1995, 6, 141.
8. (b) Sandanayake, K. R. A. S.; James, T. D.; Shinkai, S. Pure & Applied Chem., 1996, 68, 281.
9. (c) Shinkai, S.; Takeuchi, M. Trends Anal. Chem., 1996, 15, 188.
10. (d) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem. Int. Ed. Engl., 1996, 35, 1910.
11. (6) (a) De Silva, A. P.; Gunarathe, H. Q. N.; McCoy, C. P. J. Chem. Soc., Chem. Commun., 1996, 2399.
12. (b) De Silva, A. P.; Gunarathe, H. Q. N.; McVeigh, C.; Maguine, G. E. M.; Maxwell, P. R. S.; Q'Hanlon, E. J. Chem. Soc., Chem. Commun., 1996, 2191.
13. (c) De Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; McCoy, C. P.; Maxwell, P. R. S.; Rademacher, J. T.; Rice, T. E. Pure & Appl. Chem., 1996, 68, 1443.
14. (d) De Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev., 1997, 97, 1515.
15. (7) (a) Czarnik, A. W. Acc. Chem. Res., 1994, 27, 302.
16. (b) Czarnik, A. W. Fluorescent Chemosensors for ion and molecular Recognition, ed.; ACS Books: Washington, 1993.
17. (8) (a) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. J. Chem. Soc., Chem. Commun., 1994, 477.
18. (b) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem. Int. Ed. Engl., 1994, 33, 2207.
19. (c) James, T. D.; Sandanayake, K. R. A. S.; Iguchi, R.; Shinkai, S. J. Am. Chem. Soc. 1995, 117, 8982.
20. (d) James, T. D., Linnane, P., Shinkai, S. J. Chem. Soc., Chem. Commun. (Future Article)., 1996, 281.
21. (e) James, T. D.; Shinmori, H.; Takeuchi, M.; Shinkai, S. J. Chem. Soc., Chem. Commun., 1996, 705.
22. (f) James, T. D.; Shinmori, H.; Shinkai, S. J. Chem. Soc., Chem. Commun., 1997, 71.
23. (9) More recently, James et al. reported a PET chemosensor with an anthracene fluorophore appending an o-aminomethylphenyl boronic acid group and a crown ether group which selectively binds glucosamine: Cooper, C. R.; James, T. D. J. Chem. Soc., Chem. Commun., 1997, 1419.
24. (10) Preliminary communication: Takeuci, M.; Yamamoto, M.; Shinkai, S. J. Chem. Soc., Chem. Commun., 1997, 1731.
25. (11) Schauer, R. Trends Biochem. Sci., 1985, 10, 357.
26. (12) Goodman, M. S.; Hamilton, A. D.; Weiss, J. J. Am. Chem. Soc., 1995, 117, 8447.
27. 17 However, the pH correction by Bate's buffer was impossible with this buffer system. In this paper, therefore, we directly recored the "pH" values obtained with a glass-electrode pH meter.
28. (14) Forgues, S.-F.; Bris, M.-T. L.; Guette, J.-P.; Valeur, B. J. Phys. Chem., 1988, 92, 6233.
29. (15) (a) Imada, T.; Kijima, H.; Takeuchi, M.; Shinkai, S. Tetrahedron Lett., 1995, 36, 2093.
30. (b) Idem, Tetrahedron, 1996, 52, 2817.
31. (16) Bates, R. G.; Paabo, M.; Robinson, R. A. J. Phys. Chem., 1963, 67, 1833.
32. (17) Good, N. E.; Winget, D. W.; Winter, W.; Connolly, T. N.; Izawa, S.; Singh, R. M. M. Biochemistry, 1966, 5, 467.